Cleo Summers

Cleo is your work colleague and she left the hotel booking up to you, you told her you had booked a twin but it turns out you've actually booked a super king hoping that you would be sharing a bed with her but Cleo has other ideas. She makes it clear that she is sleeping in the bed alone but she is willing to make you a deal so you don't feel so bad about sleeping on the floor.

Hotel Hottie

Cleo is chilling out on the bed reading a book and you are getting a good look up her satin nightdress to her red thong and sexy bubble butt, you can feel your cock getting super hard and you know it's only a matter of time before she turns around and spots the bulge in your trousers and you wonder how she is going to react.

Keep Perving

After your very horny session with your sex therapist and your girlfriend where you all masturbated in front of each other, your next session will focus more on sex positions. Your therapist whips out a torso and begins to show your girlfriend how to deep throat by relaxing her throat. She then moves on to riding the torso explaining her techniques for a very pleasurable fuck!

Cleo Summers "Threesome Therapy: P2"

You and your girlfriend have been going to sex therapy recently, and you've discussed the idea of having a threesome. Your very attractive therapist advises you not to use a friend as it could be too close to home, so she graciously offers her professional services. She instructs you to start wanking while herself and your wifey masturbate with you... how fucking horny is this!?

Cleo Summers "Threesome Therapy: P1"

Your boss is not very happy with you. She can see you're slacking at work and now she wants to humiliate you. Demanding you to get your dick out, she wants to watch you wank as she unbuttons her blouse, revealing her juicy tits. Your boss will pull her panties to one side and show you her cunt as long as you keep jerking!

Cleo Summers "Obey The Boss"

Your girlfriend Cleo has found some knickers in the wardrobe that aren't her and she demands to know what you've been up to. You tell her that you have been keeping a secret for a while, you have a panty fetish but not the usual kind of fetish. You enjoy wearing women's underwear and the way it feels on your cock, Cleo is relieved that you haven't been having an affair and she is even willing to have some fun with you and your little fetish.

Secret Sissy

You've just had an amazing wank with Cleo whilst playing strip poker, but Cleo bet you a blow job if you won the last round... which you did of course. So now you're hard again, enjoy your hot date's lips around your cock and she want's you to cum all over her tits! What a saucy minx she is, she might be a keeper!

Cleo Summers "Frisky First Date: P2"

You're super excited about your first date with the gorgeous Cleo Summers. She's really caught your eye with her flirtatious and cheeky personality. You're playing strip poker at her place and you know where this is gonna go... with you both naked masturbating in front of each other obviously!

Cleo Summers "Frisky First Date: P1"

Cleo has been tasked with keeping you out of the jail but the only way she can do that is to stop you from being a peeping tom! Her preferred method is to let you get the impulse out of your system by letting you look up her skirt and wank, she instructs you to take your cock out and sit in front of her wanking while she shows off her panties and pussy to you.

Filthy Fucker

Does it make your cock hard having a woman dominate you and talk down to you, telling you how pathetic and worthless you are. Cleo Summers is your mistress today and you will do exactly as she tells you as you rub your worm dick while she teases you with her tiny black shiny shorts and knee high boots...

Cleo Summers "Are You Worthy?"

Cleo catches you hiding under her desk and quickly realizes that you have been trying to look up her skirt, she makes you stand up and she can't believe her eyes when she sees the bulge in your trousers. Luckily for you Cleo is in a naughty mood and wants to have a little bit of fun with you, she tells you to pull your cock out and start wanking while she teases you with her knickers and short skirt.

Under My Desk

Are you ready for your Skype call with Cleo for a raunchy cam show! She's all dressed up for you, wearing her sexy green and black lacey lingerie and it has your cock growing instantly. Cleo has come prepared as she shows off her dildo, sucking it as though it's your cock before sliding it into her wet and juicy cunt!

Cleo Summers "Cam Show"

Cleo has crashed the family car after having one too many gins and she needs you her step-brother to help her out, she is wearing a very short dress and you decide this is the best chance you are going to get to see her ass and pussy so you make her a deal. You will take the blame for damaging the car if she lets you look up her skirt and wank while she talks dirty to you and takes her panties off.

Do Me A Favour

Your yoga instructor is very beautiful and you can feel yourself getting a little bit too excited as she begins to bend over in front of you. You try and have a sly stroke of your cock, but she sees what you're doing! Lucky for you your instructor is game for some fun and starts to tease you, pulling down her tight leggings and teases you with her red thong and pussy as you wank your dick!

Cleo Summers "Spunky Session"

Getting a divorce is never fun, but your lawyer is incredibly comforting... and sexy as fuck. She can see you checking out her stockings and tells you she understands you must be feeling pent up and frustrated. Perhaps if she slipped off her dress, shows you her juicy breasts and played with her pussy while you wank your cock, it will help you move on from your bitch wife!

Cleo Summers "Legal Advice"

You're on a cleaning job with Cleo, but you're feeling particularly horny as you watch her polish the windows in her tiny denim skirt. But Cleo hasn't brought you along on this job to have you perve on her... what will it take for you to stop being so devilishly distracted?...

Chance Of A Lifetime

Your work is offering you some support at the moment. You're feeling down and need to express your frustrations, and Cleo is here for you to listen and help. She wants you to relax and get real comfortable, but you're able to catch glimpses of her red panties up her skirt, along with the tops of her stockings. You're hard as hell and she knows it...

Cleo Summers "Let's Get Comfortable"

Cleo is your step-mum and she has noticed that some of her underwear has gone missing, she knows that you have been going through her drawers and wanking into her knickers so she wants to make you a little deal. She is going to let you look up her skirt at the knickers she is wearing while you take your dick out and wank in front of her! This is the chance of a lifetime so you best give Cleo your best performance!!

Brace Yourself

Your step-mum Cleo isn't happy about you having a girl around but you have a trick up your sleeve, you know Cleo has some naughty videos on the internet and you threaten to tell your dad if she doesn't agree to let you have your girlfriend round. Your plan backfires spectacularly though when Cleo tells you that your dad already knows about the videos!

Earn It My Way

You're auditioning for a new porn star, and today you'll be seeing the very sexy Cleo Summers on your casting couch. She'll be showing off her deep throating skills on all the dildos you've supplied for her. She'll finish off her audition by fucking herself from behind and deep throating a toy at the same time! Impressive stuff!

Cleo Summers "Casting Couch"

Your cleaner is unware you're home and she's on the phone to her sister slagging you off! Once she's realised you've heard her phone call, it's all very awkward. She decides to work her charm and try and get back into your good books by teasing and flirting with you. You love her tight leggings and the way she strokes her pussy while you jerk you big dick!

Cleo Summers "Perving On The Cleaner"

Cleo is such a vixen, sat there relaxing without a care in the world. She knows exactly what she is trying to do to you, sneakily moving her legs around so you can see right up her skirt. She isn't even wearing any knickers so you can literally see everything she has to offer. This is a bit taboo though, she is your step-mum, but why pass up on a chance like this though with a gorgeous older woman.

Surprise Flash

Cleo has called you over because she knows you're a bit of a handy man, and her bed needs fixing. It's a little bit awkward because you've recently broken up with Cleo's best friend, but you sense she's up to no good as she lays on the bed in her little black dress and heels... and she seems to be wearing no panties too...

Cleo Summers "High Sex Drive"

You've just got back from dinner with your brother and his wife, and your brother has passed out upstairs. Cleo is waiting for you in the bedroom and is eager to see your cock again, but this time she'll do much more than watch you wank it. She can't wait to wrap her mouth around your delicious dick and to fill it inside of her soaking wet pussy!

Cleo Summers ‘My Brothers Wife: Pt2’

You are a bad bad boss, always wanting to flirt with the sexy employees of the office. There is none sexier than Cleo either, she stands out like saw thumb when she wears that low-cut blouse which shows off her amazing bosom. She is a bit freaky as well and knows that you like it when people sweet talk you, making your dick harder than anything. All you need is for it to blow off in front of her.

Bad Bad Boss

You've sneaked into your sister-in-laws bedroom to grab a glimpse of Cleo in her sexy lingerie. She look so hot, you're so jealous of your brother having such a beautiful wife. She catches you perving, but allows you to watch her try out some outfits for the dinner you're all off to tonight, help her decide on what to wear. But you're so turned on, and she's not blind, she can see you're huge bulge through your trousers...

Cleo Summers ‘My Brothers Wife: Pt1’

Cleo is busy cleaning the stairs and you are busy ogling her whilst looking up her skirt. You notice that she has a very revealing hole in her tights, right where he pussy is and it's making you hard. She catches you out but seems to like it, she makes the hole even bigger, so you can see her whole pussy. It's gorgeous, perfectly succinct, and raring to go, waiting for your heavy cock and balls.

Tearing a New One

This Milfy cleaner is a lovely bit of eye candy to look at whenever you stay at this hotel, she also has these great big pair of tits, and she doesn't like to cover them up. Cleo - that is the pretty little lady's name - can be a bit dirty as well, something that you will soon find out about as she is calling you over, calling you to ogle at her tits whilst she sweet-talks your semi-hard cock.

Milfy Cleaner

Your lack of wanking ability is getting silly now and you need Nurse Summers to help you with your jerking techniques. She will demonstrate on her model for you, and your cock seems to be incredibly excited by Nurse Summers uniform, with her white stockings and sexy glasses, this is surely going to be the best wank you've ever had! Especially when Nurse Summer shows you her juicy tits and spreads her legs wide open for you!

Cleo Summers ‘Control Your Cum’

Usually, when you stay at this hotel it keeps itself at a good standard. This time though, you have found some problems and need them sorting. Cleo (the manager) comes to take a look, but instead of fixing the leak, she will make you leak out of your cock, just so you won't give the place a bad review. Cleo is a sexy older woman and knows just how to sweet talk to you when the right time comes.

Stick and Lick

You're about to get hitched, but the maid of honour has something to say about that. She tells you to run as far as you can and be a free and single man, that her best friend only wants you for your money. You've secretly always had a thing for Cleo and she seems to be hungry for you COCK. She's taking off her dress, revealing her cute thong and sexy stockings, getting on her knees to fill up your mouth with your delicious dick...

Cleo Summers "Maid Of Honour"

You've ordered a Stripagram to your hotel room, and your cock instantly begins to grow when Cleo Summer comes walking through your door. She's quite the dancer and you love her playful outfit! After she's finished dancing for you, you request to wank over her and cum all over her juicy arse, but that will be extra!

Cleo Summers "Stripagram"

It is time for your daily work call with your assistant Cleo, fingers crossed she is wearing something very revealing again so you can ogle at her magnificent bosom again. It is the only reason you actually hired her. As soon as she answers the call you can see her breasts poking out of her shirt, they could have your eye out they're that big. Try and finish the meeting off if you can.

Finish Yourself

Your brother has been married to Cleo for over a year and Cleo thinks he's getting bored with her and might leave her! Cleo really wants to spice it up in the bedroom in the hope he doesn't leave her. You been the perve you are, suggests she buys herself a dildo to use in the bedroom with him. But what better way to test the dildo out than get Cleo to ride it in front of you. Get your COCK out and JERK it as Cleo's tight lips bounce up and down on the dildo!

Cleo Summers "Testing Out My New Sex Toy"

You've turned up to Cleo's house to get your overdue rent money but she doesn't have it. She suggests if she can repay you in another way, you've liked her for a long time so this is the perfect compromise. Watch with your COCK in your hand as Cleo plays with her juicy pussy on the bed and then gets out her pink dildo and starts FUCKING her tight hole! She really wants to repay her debt to you.

Cleo Summers "Masturbating For Free Rent"

You've been called back into your teacher's office to talk about your erotic writing. As inappropriate as it was, you've made your teacher, Cleo, really horny...and now she wants to give you some proper inspiration for your erotic writing. Get your COCK out and let Cleo suck and fuck you until you explode. You won't ever have writers' block again!

Cleo Summers "Teacher's Pet Pt:2"

You are off out to meet up with a girl…again. Your step mum, Cleo, isn’t having any of it! She’s tired of you always sneaking out to sleep with girls and she thinks you need a proper woman. Get your COCK out and JERK it over Cleo as she shows you her amazing body and amazing tits. Cleo wants to show you what a proper woman looks like!

Cleo Summers “Step Mum’s Order”

You're plumbing over at a clients house... When you get there, you didn't expect her to be this stunning! You get straight to work though - the kitchen sink is fucked and you have to have a look at the pipes under the sink... But while you're on your back looking at the pipes, the client starts walking around the kitchen and she's wearing a super short skirt - so short that you can see right up her skirt.

Like What You See?

Cleo has asked to see you, she has booked 2 nights to stay in your hotel but there seems to have been a mix-up. She has been told she has only booked one night and wants to sort it out, you quickly notice she is wearing a very revealing top and her enhanced tits are barely being covered. You decide to take advantage of the situation and tell her that you can help her out if she agrees to let you wank over her tits.

Jerk Over Me

You need to see your boss to discuss important work related stuff. However, Cleo, his wife, won't let you up to see him as she is waiting for him to finish for the day as they've got a planned meal. However, you won't leave unless she does something for you. Watch as your bosses WIFE gets her pussy out and plays with it whilst your boss is working upstairs. Naughty fuckers! She wants you to blow your load over her hot body.

Cleo Summers "Wanking Over Your Bosses Wife"

You've brought your step-daughter Cleo away for the weekend... When you get to the place you're staying there's a lovely fireplace with some fresh logs to burn... Cleo gets right on getting the fire started, but while she's starting the fire you can't help but look up her skirt! What a lovely weekend away with your step-daughter this is going to be.

Got Wood?

You are Cleo's favourite student! She has brought you into her office today to talk about your EROTIC literature. She knows that you've written it about her and she wants to give you some more inspiration! Cleo wants to give her favourite student the best writing help in your next erotic tales. She wants you to get your COCK out and wank it over her as she spreads her pussy lips for you. Listen to teacher!

Cleo Summers "Teacher's Pet Pt:1"

Cleo is cleaning your stairs and you are getting a good look up her dress, she is wearing a summer dress that is so short you can see her ass and thong. It doesn't take Cleo long to notice you looking and she quickly realizes what a dirty old pervert you are, you requested that she wear a dress and know she knows why!

Dirty Old Man

Cleo has been a good estate agent to you. She really wants you to buy this house, she will do anything for her commission. She wants to look after you and make sure you're making the best decision. Get your COCK out and jerk it over this sexy estate agent as she shows you her tight little pussy and perky tits! Surely, this will persuade you to buy the house?

Cleo Summers "Dirty Estate Agent"

Cleo has noticed that when her friends are around you are always trying to get a look up their skirts, she has decided today to put an end to it.  You clearly have a panty fetish and your step-sister Cleo is going to help you out, she wants you to get your dick out and start wanking while she teases you with her panties and pussy!

Stroke It For Your Step-Sister

Cleo is looking for her keys, she is running late and needs to find them. She asks you if you have seen them and she quickly realizes you have them, she catches you looking up her dress and it doesn't take her long to figure out what you're up to. Cleo knows in order for you to hand her keys ove4r she is going to have to let you wank over her panties and pussy!

Wank It Out Of You

Cleo is your girlfriend’s housemate…but this doesn’t stop you from perving on her whilst she’s taking a bath and fucking her tight little hole with her glass dildo, oh what you would do to fuck her. Cleo doesn’t mind you watching her…get your COCK out as she makes you rock hard whilst she fucks herself!

Cleo Summers "Playing In The Bath"

Cleo is trying to get the house cleaned up before your parents get home, she is fed up of being the only one who ever does anything around the house. She is wearing a summer dress and when she bends over you can see her ass, you are always fantasizing about your step sister and you even steal her knickers to wank in when! It doesn't take long for her to notice you perving on her and luckily for you she is willing to make you a deal, she will let you look up her dress and wank if you agree to get off your ass and help her clean the house.

Do You Like That?

What a dirty pervert you are! Watching your step mom as she has a shower. You’ve always wanted to see her perky arse and massive tits, well now is your chance! Your dad is working, and you are off college so get your COCK out and jerk it for your step mom as she spreads her juicy pussy for you.

Cleo Summers "Perving On My Step Mom"

Cleo is dressed up for a night out with the girls, she is wearing a little black dress and wants to know if it's too short, you tell her to bend over and realize you can see her knickers. She assures you she isn't going out on the pull and to make you feel better about her going out without you she suggests you have a bit of naughty fun together before she leaves.

Is This Too Short

Cleo is relaxing after a hard day at work reading the book she borrowed off you, when you got to get it back she tells you she wants to carry on reading. You decide to hand around while she does and get a look down her dress, she has perky enhanced tits and you can't help but get a boner. Cleo realizes what you are up to and decides to make you a naughty deal.

You Owe Me

Cleo come into the bathroom and starts cleaning, she is wearing a very short denim skirt and when she bends over you can see her white thong, it doesn't take Cleo long to notice you staring at her ass and luckily for you she is in a naughty mood. She knows that you have been stealing her knickers so she decides to let you have a wank now if you agree to give them back to her.

Cleo Summers

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